Aniline → HCID 11345649, compound

HRID 898830Notes

Reaction equation

HRID 898830 reaction equation
[C:1]([N:6]1[CH2:10][CH2:9][O:8][C:7]1=[O:11])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.FC(F)(F)S(O)(=O)=O.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[C:13]1([NH:12][CH:3]([CH3:4])[CH2:2][C:1]([N:6]2[CH2:10][CH2:9][O:8][C:7]2=[O:11])=[O:5])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 62406Trifluoromethanesulfonic acidHCID 5365845HCID 5365845, compound

Product 1

HCID 11345649HCID 11345649, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-crotonoyl-1,3-oxazolidin-2-one (47 mg, 0.3 mmol) and Pd((R)-binap)(H2O)2(OTf)2 (8.0 mg, 0.0075 mmol) in toluene (1.5 ml) in a stream of nitrogen was cooled to 0° C., and aniline (42 mg, 0.45 mmol) was added. To the solution was dropwise added trifluoromethanesulfonic acid (63 μL, 0.45 mmol), and the resulting mixture was stirred at room temperature for 24 hours. When no starting material was detected, a saturated aqueous solution of ammonium chloride was added to quench the reaction, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated and purified by a silica gel column chromatography (hexane:ethyl acetate=1:1) to give the objective 3-(3-phenylaminobutyryl)-oxazolidin-2-one (66 mg, 89% yield). The enantiomeric excess ratio was determined to be 94%. e.e. by a liquid chromatography with an optical isomer separating column (column: AD-H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. custompurified by a silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0fb49a1aa47042f48458837acf0ca3c9
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

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